


First Time

by VioletPony



Category: Henry Stickmin Series (Video Games)
Genre: Angst and Fluff and Smut, Bottom Henry, Fluff and Smut, Hurt/Comfort, M/M, Missionary Position, NSFW, Poor Henry, Scar Kissing, Scars, Smut, Special BROvert Ops Ending | SBO (Henry Stickmin), Top Charles
Language: English
Status: Completed
Published: 2021-02-08
Updated: 2021-02-08
Packaged: 2021-03-13 16:47:55
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,898
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29281716
Author URL: https://archiveofourown.org/users/VioletPony/pseuds/VioletPony
Summary: Henry and Charles have been dating for a while and have been trying to take their relationship to the next level. Both of them want to take their relationship further, but Henry has always stopped them before they have gotten too far. While Charles has respected this, he's still confused and wonders: "Why is Henry so afraid to have sex with him?"The two attempt to try again tonight. Maybe the ending result will turn out differently this time...
Relationships: Charles Calvin & Henry Stickmin, Charles Calvin/Henry Stickmin
Comments: 19
Kudos: 63





	First Time

**Author's Note:**

> This turned out longer than I meant it to be, but I'm not complaining, lol. Hope you all enjoy this very fluffy Stickvin smut. :)

"It's alright, Henry. We don't have to do this..."

"B-But, I want to do this!"

The couple had been in an intense make-out session on Charles' bed a moment ago, that was before the ace pilot had slowly slid his hand up Henry's shirt, causing the ex-thief to jump back a little. They had been trying to get to the next level of their relationship for a few days now, and each time Henry had backed out, which was fine in Charlie's eyes, but he just didn't understand why Henry was so afraid.

"Baby, there's no rush if it makes you uncomfortable," The pilot stated. "We can wait to do this."

Henry groaned a little in frustration. "But I don't want to wait anymore! I...I want to do this, I really do, but..."

Henry grew quiet, appearing to be too embarrassed to finish his sentence. Charles waited momentarily before scooting closer to him, placing a comforting hand on Henry's knee.

"But...?" Charles offered, trying his best to comfort his boyfriend.

"But..." Henry sighed lightly before looking away. "I'm scared..."

Charles's soft expression turned into a melancholy one. "Oh Henry, it's alright. It's normal to be worried if it's your first time-"

"-That's not what I meant," Henry interrupted. Charles was confused again. "I mean...it will be my first time, but that's...that's not why..."

Charles attempted to think of another reason why Henry would be scared of having sex other than the fear of sex itself, but thankfully he didn't have to think too long, as Henry exhaled before elaborating.

"It's...It's because of my body...I have a lot of...scars."

The ex-con still wasn't looking at his lover, too embarrassed of himself to simply turn his head towards him. Charles wanted to fix that, especially now that he knew why the other man was so afraid. The military man gently cupped his boyfriend's cheek, turning it so that Henry was looking at him again, causing the other to blush a little.

Charles made sure to speak softly as if he was scared that Henry might run off like a wild animal at the slightest loud noise.

"Hen, look at me, alright? There's something I wanna show you." Henry nodded a little, not really knowing what to expect.

Well, he DEFINITELY didn't expect Charles to start taking off his shirt. The smaller man's face turned bright red as the pilot removed his shirt, exposing his toned muscles and abs from years of working for the government, and...scars...huh. Henry's expression changed from extremely flustered to questioning. Charles has scars. He counted about 7 of them.

"See? I have some too," Charles said with a soft smile as he traced his fingertips over a few of them. "Scars aren't bad or ugly, Hen. It shows all that you've been through, all that you've accomplished and lived through."

Henry quietly stared momentarily before averting his eyes. "...There's a difference between your scars and mine, Charles..."

Charles frowned as Henry continued his statement.

"You've gotten your scars from protecting the law...I've gotten mine from breaking it. You're a government pilot who helps protect and save people...I...I've hurt people, a-and I'm a terrible-"

Charles quickly grabbed Henry's cheeks, turning him so that they were face-to-face, only about a couple of centimeters away from touching.

"-No, Henry. You aren't. All of that's in the past now."

Henry's eyes started to water. "But-"

"-I don't care what you've done in the past. I only care about who you are now, and you are not a heartless crook. You're a fun and supportive man who cares about his friends and loved ones. You're a loveable kleptomaniac who has a good heart...You're the man I fell in love with, so don't you ever think that you are a terrible person...You're my Henry."

The other man was crying now, quickly pulling Charles into a hug. He rested his head onto the other's bare shoulder and cried softly as his boyfriend rubbed his back.

"You're a good man, Hen...and I love you, don't you ever forget that..."

"I-I love you too," Henry said, still holding onto Charles for dear life.

Charles started to gently rock him, continuing to rub his back. They stayed like this for a few minutes before Henry sat up and wiped his eyes.

"You alright?" Henry nodded, staying silent for a moment before speaking.

"I...I think I'm ready."

Charles' eyes widened at this. They had just had a big emotional moment. Henry had just been told (probably for the first time in his life) that he was a good person, and that his past scars mean nothing to Charles. And now he wants to try again right away? Charles didn't think this was a good idea, but...it was what Henry wanted. Still...

"Henry, are you one hundred percent sure?" Charles asked carefully, worry spread all over his face. "I'm completely fine if you wanted to wait still, you don't have to-"

"-Charles." Henry interrupted, placing a hand on his lover's shoulder. He still seemed a little embarrassed, but more sure of himself.

"I...I know I might not be the most...comfortable with my body right now, but...I trust you, Charles. I've never trusted anyone else before...but I trust you, and I love you. I know that you'll be gentle with me, and help me if I need it..."

Charlie's worried face slowly turned to a warm smile as Henry spoke. He kissed Henry's forehead before replying.

"Alright, Henry. I love you too."

Henry's heart skipped a beat as his cheeks started to turn a light shade of red. The warm smile of his face matched Charles' as they gazed at one another momentarily before Henry leaned in for a kiss.

The taller man immediately kissed back, but the small little smooches soon turned into a passionate make-out session as soon as Charles slipped his tongue into Henry's mouth. As their tongues danced, Henry felt hands wrap around his waist, and before he knew it he was pulled onto Charles' lap, accidentally letting out a quiet squeak. (which Charles totally heard and thought was adorable). Henry's face flushed as Charles giggled.

"You're adorable."

Henry only covered his face with his hand in response, his face clearly red even in the dimly lit room. Charles then started planting small kisses on Henry's cheeks and neck, making the other man move his hands away. Yes, he was still very flustered but who wouldn't want kisses from Charles?

After a minute or so, Charles stopped giving little kisses and started to suck on Henry's neck, making the man shiver.

"M-Mm...Charles..."

Charles ran his hands along Henry's still clothed body, continuing to suck and even nibble on his neck. The smaller man grazed his hands over Charles' muscles, tracing a few of his scars. Henry's face turned a darker shade of red when he realized he was hard. He could also feel something poking him, blushing even more when he realized that he wasn't the only one who was excited...

Fuck how long had it been since Charles started sucking on Henry's neck? Henry had no idea, but right now he didn't care. He was loving this. The feeling of being kissed and licked over some of his most sensitive areas turned him on immensely, and it honestly made him feel loved.

He felt Charles pull away from his neck, most likely now covered in marks, and look up at him as he tugged on his shirt.

"May I?" He asked, wanting to make sure Henry was still alright with it.

Henry slowly nodded in response. He was ready. He could do this, it wasn't a big deal. He trusted Charles, and Charles was right. He shouldn't dwell on marks of his past. He was better now. He was working with the government. All because of Charles. Charles was the one that made him want to switch sides, the one who didn't care about his past, the one who wasn't afraid of him. The one he fell in love with, and he trusted the man with his life.

Henry lifted his arms up as Charles started to take off his shirt. He quickly shut his eyes, still feeling embarrassed about his scars. Once Charles took off his shirt, Henry set his arms back down but kept his eyes closed. There was a part of him that was still worried about how Charles would react. After a few seconds of silence, Henry felt a soft touch trace over the lower part of his neck. The man opened his eyes to see his boyfriend tracing over his largest scar, the one of his neck, with a melancholy expression. Henry frowned, about to ask if he was alright before the other leaned down and kissed his neck, right over the scar.

Henry blushed as he let out a small noise purely out of shock. Charles pulled his boyfriend closer to him, kissing the neck scar a few more times before moving on to some of the others. Henry didn't know what to do, but he knew this: He loved it. The amount of attention, the amount of love was almost overwhelming. Even though they're just small little kisses, they meant the world to Henry.

After giving what felt like one hundred kisses, Charles sat back up, momentarily looking into Henry's eyes before gazing back down at his body.

"How...many are there...?" Henry was a little hesitant to answer, not because he was afraid...but because he knew the answer.

Henry averted his eyes before speaking.

"...22."

He didn't even have to see Charlie's face to know that he was upset by that answer. He felt his boyfriend's hand brush over his chest before he felt him kiss his neck.

"You're body's gorgeous, Hen..." The pilot said before looking back up at Henry, their eyes meeting as Charles cupped his cheek. "I love you so much, and your scars only make you more beautiful to me..."

Henry smiled as his face grew red. Fuck how the hell did he get this lucky? How did he, an ex-thief who had a criminal history, get to be with the kind, affectionate, and caring government pilot? Honestly, he didn't care. He was happy.

He pulled the taller man into a passionate kiss, wrapping his arms around the other's neck and letting them rest on his shoulders. Charles immediately returned the kiss, placing his hands on Henry's waist. The two of them held each other close, neither one of them wanting to let go.

After a minute or so, Henry felt Charlie's tongue enter his mouth, moaning a little as he started sucking on it. The pilot slowly moved his hands down from Henry's waist to his hips, soon turning a little to cup and sneeze his ass, causing the man to let out a surprised squeak. Henry could practically feel Charles' smirk on his mouth. That little fucker. He's lucky that he loves him.

As much as he wanted to continue kissing Charles, Henry broke the kiss, a trail of saliva connecting their tongues. The ex-con blushed as he wiped his mouth, looking away as he spoke.

"H-How-" He quickly cleared his throat, "How do we...you know...wanna do this...?”

Henry mentally smacked himself for acting like this. He was a fucking badass criminal for Pete's sake! Now he's stuttering and embarrassed like a schoolgirl talking to her crush. Charles only smiled at him.

"Whatever you want, Henry...I could top if you want, or I could bottom."

Henry was honestly torn. He would love to be on top of Charles, hear him moan out his name in such a submissive way...On the other hand, he would also love for Charles to be inside of him. Fuck, he almost got chills at the mere thought. Besides, he didn't know how to top, and he didn't want to accidentally hurt Charles.

Alright, that settled it.

"I...I can bottom..." Charles nodded a little, giving his lover a quick kiss on the cheek.

"Alright, I'll be gentle. I promise." Henry shivered a little at that.

"O-Okay."

Charles gave him one last reassuring kiss on the cheek before going to his mouth, Henry quickly kissing back. Soon, Henry felt the other man's hand graze over his chest, slowly going down to his stomach, and stopping on his semi-hard bulge. Henry moaned into the kiss as Charles started to rub it, feeling his face heat up immensely. Fuck, he had masturbated before, but having someone else touching you is such a different feeling.

Henry slipped his tongue into his lover's mouth as he moved a hand down to Charlie's bulge, starting to rub it as well. Damn, it was hard, it felt big too. Henry didn't have much time to think about Charles' size, however, as he felt his sweat pants being taken off. Charles, however, could only get them down to his knees because of their current position.

"Lay down on your back for me, Baby?" Charles asked in a soft husky tone that honestly drove Henry mad.

He quickly obeyed, scooting back a little bit before laying down with his back touching the soft bed sheets. Charles pulled the pants off the rest of the way, noticing Henry also had some scars on his legs. The pilot pushed that aside though, he didn't need Henry to catch him staring and make him feel self-conscious. He wanted him to feel good, and that was his plan. His greatest plan.

Charles looked up at Henry as he placed his hands on the other man's boxers, wanting to make sure he was alright with it. Henry blushed but nodded at him, so Charles took that as a sign to continue. He took off the man's black boxers to see his lover's very erect dick, causing both men to blush for different reasons. Henry felt a little exposed at the moment. No one has ever seen him like this, and he was a little embarrassed. Charles on the other hand couldn't be more turned on.

Henry was pretty big, not as big as Charles, but still big and definitely thick.

Charles trailed his fingers over the tip before wrapping his hand around it and slowly pumped, causing Henry to twitch a little and let out a soft moan. He smirked a little at how submissive Henry was being. It was a whole other side of him that Charles couldn't wait to see more of.

He stopped the hand job momentarily to spit onto his hand before moving back to his lover's cock, making it much easier to move his hand and feel much better to Henry, and yes he could tell. As his pumping started to get faster, Henry's moans started to get louder and more frequent. While he loved watching him enjoy himself, this wasn't the end of his plan. After a moment he stopped pumping, moving away from Henry's dick to get some lubricant from his drawer causing the man to whine a little. His sadness, however, was quickly replaced with confusion as Charles squirted some of the lube onto his fingers.

"What's that for...?" Henry asked.

Charles looked a little confused before he understood what Henry was asking. Damn, the poor guy didn't even know what lube was or what it was for.

"It's lube. It's to make it hurt less." Charles noticed that Henry wasn't exactly calmed by this answer, in fact looking even more nervous.

"Hurt less...?"

Charles kissed Henry's forehead before sitting down in front of him, rubbing his boyfriend's thigh with his non-lubricated hand.

"Don't worry, Hen...I'll be gentle, remember? It might hurt a little at first, but that's normal." Henry nodded a little, still a little nervous but he trusted Charles.

"Good," Charles said before positioning a finger in front of Henry's entrance. "Just relax, Baby.~"

Henry sucked in air through his teeth as Charles pushed a finger in. This was definitely a weird feeling and a little painful...but not too bad. Henry moaned a little as the finger started going in and out, quickly getting used to the feeling.

"You want another?~" Charles asked in that same husky tone as before.

"M-Mhm..."

Henry gasped as another finger entered him. It hurt a little more, but it also felt good. Charles thrusted slowly before he started to make scissoring motions, making Henry moan even more.

After a minute or so of fingering, Henry felt like he was ready. He needed Charles inside of him now.

"C-Charles...P-Please..."

The ace pilot stopped fingering him for a moment. He knew what Henry wanted, but Henry didn't know that, and he wanted him to beg.

"Hmm? Yes, Hen?"

"I-I need you...inside me. N-Now." Charles smirked.

"Alright, Baby.~" He said before quickly pulling out his fingers, causing Henry to let out a small grunt.

Charles shifted a little on the bed as he tried to get his pants off, Henry watching with hungry eyes.

Holy shit.

If Henry had thought Charles was big before with that bulge in his pants, then he apparently hadn't seen anything until now. It looked about 8 inches long, and Henry was practically drooling. Nope, scratch that, he was definitely drooling. Charles noticed this, smirking a little as he spoke.

"Like what you see, Baby?~"

Henry, only now realizing how much he was staring and that Charles noticed, blushed and looked away but nodded a little. The taller man chuckled as he crawled on top of him, kissing his neck a little.

"You're so cute."

Henry only groaned a little in response.

"Aww, c'mon," Charles said. "Where's that beautiful voice I love so much?"

Henry tried to remain silent but he gasped and moaned as he felt the fingers re-enter his hole.

"There it is.~" Mother fucker-He'd kill this man if he weren't so hot.

Charles felt satisfied enough to pull out his fingers and stop teasing him. He shifted his body so that the tip of his dick was touching Henry's entrance.

"Remember, just relax. I'll make sure my Baby feels good, alright?"

Henry's heart skipped a beat at that, he quickly nodded. As Charles slowly pushed in, Henry groaned a little. Fuck it felt so much bigger than it was and it wasn't even fully in yet. Charles stopped pushing halfway, waiting for Henry to get used to the feeling for a moment.

"You...can move..." Henry huffed.

Charles slowly pulled out and pushed back in again, causing Henry to groan again. It was quieter though, and he was starting to get used to it. Once most of the pain was gone he couldn't help his volume. Granted he wasn't screaming but ohh Charles was definitely gonna fix that.

The ex-con was currently a moaning mess under the pilot, so when Charles pushed all the way in it made him yell. He quickly covered his mouth, embarrassed by how loud he was being, but he couldn't help it. With Charles thrusting all the way inside of him. Fuck, how could not scream? Charles, on the other hand, had a different plan. He forcefully moved Henry's hands away from his mouth, pinning his arms down as he continued to thrust.

"Uh-uhh...I want to hear your voice... ~"

Henry's heart was pounding. He couldn't hold the screams in anymore, but if Charles wanted to hear his voice so badly then he would give it to him. He moaned louder at each thrust, and even louder when Charles started to speed up. He didn't even care about his arms being pinned down, honestly, he kind of liked being restrained. Fuck, he loved this so much. He loved Charles being inside of him, and he loved being on bottom-embarrassment be damned.

"Fffuck, Charles! A-Ahh.~" Henry knew that the other man was turned on by that, mainly because after he moaned it Charlie's speed increased.

"S-Shit, say my n-name again.~"

"C-Charles-AAH!!!~"

Suddenly, the pleasure Henry was feeling practically doubled. His eyes rolled back into his skull as he screamed. His tongue was hanging out, dripping some saliva onto his chest. Oh fuck, wait, was that his prostate? Shit, that's what it felt like? Either way, Charles realized what he hit when Henry screamed like that, and he smirked a little as he repeatedly made an effort to hit that exact spot.

"Aah! C-Charlieee-F-Fuck!"

Henry almost felt light-headed with pleasure. He didn't care anymore about what he was saying, he couldn't think.

"Mmm...Feel good, Baby?~"

"Y-Yess!!"

Charles was pounding into Henry as fast as he could. Charles was huffing and moaning, and Henry was a screaming mess. The pilot was still holding his arms down, unknowingly gripping them tightly as he thrusted but Henry still didn't care, he was on cloud 9.

After a few more minutes of sweet ecstasy, Henry felt like he was going to explode, in a good way.

"Aa-What-*huff*-I f-feel weird-"

Charles slowed down a little so Henry could actually talk.

"F-Feel like I'm-mmm-gonna explode.~"

The taller man smirked as he realized what Henry was experiencing, quickly speeding up his pace again, making Henry yelp in pleasure.

"You're close, Hen...To orgasm.~"

Oh fuck, that's what that was? No wonder he felt like he was going to explode. He-oh god-fuck Charles found that spot again. Now he was really close, he could feel it.

"C-Charles!! F-FUCK!-"

Henry screamed as he released over his stomach. Charles was close behind him, pounding into his lover a few more times before cumming inside of him.

They stayed in those positions for a moment, gasping as they desperately tried to catch their breath. Charles pulled out slowly as he stared at his work. Henry's eyes were slightly opened, but he was looking up-almost as if he was dead. He was breathing slowly with his tongue hanging out, almost panting. Yep, Charles was proud. Operation: "Make Henry Feel Good" was a success. He did notice that there were marks on Henry's arms from where he had held him down. He felt a bit bad about that...

"You alright, Hen?" Charles huffed.

Henry only responded by shutting his eyes completely, putting his tongue back into his mouth, and mumbling a soft and elongated ‘Mhmm’. Charles chuckled softly. Yeah, he was fine, probably better than fine.

The pilot slowly lying down next to his boyfriend, wrapping his arms around him as the two of them basked in the afterglow. Henry smiled a little as he cuddled into Charles, wrapping his arms around his waist.

"So, how was it?" Charles asked as he rested his head on Henry's.

Henry huffed. "How...*huff* How do you think?"

Charles chuckled a little as he kissed his lover's forehead, running his fingers through the other man's hair.

"I'm glad...I love you, Hen."

"Love you too, Charles..." Henry yawned a little as he closed his eyes and relaxed into Charlie.

Yeah, he was definitely gonna feel this in the morning, but they were off tomorrow so he'd be fine. Charles shifted a little to pull the bedsheet over the two of them. He kissed Henry's forehead again.

"Goodnight, Baby."

But Henry had already passed out. Charles huffed softly before closing his eyes. He loved this man so much, and he couldn't wait to have more nights like this one.


End file.
